Aerial view of St. Michaels, Maryland.

7 Small Towns In Chesapeake Bay Were Ranked Among US Favorites

The gorgeous Chesapeake Bay, America's largest estuary, has a shoreline of over 11,000 km2 running through six American states. Dotting this coastline are numerous small towns brimming with scenic natural beauty and abundant tourist attractions. Here, one can find not just some of the best water-based activities in the country but also many charming downtown areas, historical landmarks, nature preserves, great seafood options, and much more. Here are some of the country's most favorite Chesapeake Bay small towns to experience it all.

St. Michaels, Maryland

St. Michaels, Maryland
The harbor at St. Michaels, Maryland.

The historic waterfront town along the Miles River of the Chesapeake Bay watershed has been a tourist magnet since the 19th century. The town's rich heritage can be best explored at the Chesapeake Bay Maritime Museum, covering 18 acres along the waterfront in a place that once was a thriving maritime trade hotspot. The 1879 Hooper Strait Lighthouse is also located here. There are also many parks and trails in and around the town, like Muskrat Park and Hollis Park, that are great for strolling with an ice cream in hand and a charming conversation partner on the side. Boat cruises are also a great way to spend the evening in this small town. And for those with a daring heart, there is also the Chesapeake Ghost Tours for a thrilling night out.

Irvington, Virginia

Rappahannock River, Irvington, Virginia
Rappahannock River, Irvington, Virginia. Image credit: David Broad via Wikimedia Commons.

Irvington, sitting cozily along the banks of Carter's Creek as it flows into the Rappahannock River, is the perfect vacation spot for tired souls. The tranquil atmosphere of this small town, the beautiful waterfront with its scenic views, the boutique stores and galleries dotting the downtown, and the delectable seafood delicacies like the Rappahannock River oysters and Chesapeake Bay blue crabs - all make the vacation a truly memorable one. For history lovers, the Mary Ball Washington Museum and the Steamboat Era Museum are a must-visit. Outdoor people can take a boat cruise down the river or embark on nature trails at the many natural preserves and parks in and around the town. Events like the Irvington Farmers Market, Turkey Trot, and Sailing Regatta are also great crowd-pullers.

Deltaville, Virginia

Lightning Over Pier in Deltaville, Virginia
Lightning over the pier in Deltaville, Virginia.

Aquaphiles will love this beautiful Chesapeake Bay town full of attractions and activities to keep them busy, like swimming, fishing, sailing, and much more. However, the town, carrying the label "The Boating Capital of the Chesapeake Bay," takes boating to another level, with over 35 marinas and service facilities! Deltaville also has a rich boatbuilding and watermen history that can be best understood at the Deltaville Maritime Museum. The adjacent Holly Point Nature Park is a great place to stretch your legs and spend some time in the tranquility offered by the surrounding greenery before you end your day dining at one of the many lavish seafood restaurants dotting the town.

Oxford, Maryland

Aerial view of Oxford, Maryland on the Chesapeake Bay
Aerial view of Oxford, Maryland on the Chesapeake Bay.

One of Maryland's oldest towns, Oxford, has a prosperous past when it served as a significant port of entry to the state and was surrounded by flourishing tobacco plantations. It is strategically located at the mouth of the Tred Avon River, as it empties into the Choptank River, a major tributary of the Chesapeake Bay. Thus, one of the best ways to experience the town is via a joyful 20-minute ride on the Oxford Bellevue Ferry, which claims to be America's oldest privately owned ferry service, operating since 1683! Other notable attractions in the town include the Waters Edge Museum, the Oxford Library, and the John Wesley Preservation Society. Outdoor lovers simply must explore the Oxford / St. Michaels Bike Trail, which is known to be one of the best of its kind in the American mid-Atlantic region.

Onancock, Virginia

Market Street in Onancock, Virginia. Editorial credit: John Blottman /

Located on the shore of east Virginia, the small town of Onancock traces its origin to 1680 and is thus steeped in history. Historical landmarks like the Ker Place and museums like the Eastern Shore Historical Society and the Eastern Shore Maritime Museum are among the best places to learn about the town's past. Moreover, there is also a lively art scene with art displays and antique shops dotted between the many seafood restaurants. The nearby Onancock Creek offers many outdoor activities like fishing and boating and is famous for its beautiful sunset views. The adventure continues to the Savage Neck Dunes Natural Area Preserve and Chesapeake Bay Bridge Tunnel, waiting to be explored by outdoor lovers.

Cambridge, Maryland

The marina at Cambridge, Maryland.
The marina at Cambridge, Maryland.

Enveloped in natural beauty, Cambridge holds many attractions to explore in its serene environment around the Chesapeake Bay area. Visitors can explore the local wildlife in the Blackwater National Wildlife Refuge or go boating alongside the waterfront. For those who love history, there's also the Harriet Tubman Underground Railroad Visitor Center, where one can learn about the role of Cambridge in African-American history. The rich culture and history of the town are also portrayed through the many artistic shops lining the downtown and waterfront areas and the lovely food served in places like the Portside Seafood Restaurant, which serves delectable American chow and seafood.

Urbanna, Virginia

Urbanna Creek, Urbanna Virginia
Urbanna Creek in Urbanna, Virginia. Image credit: C Watts via Wikimedia Commons.

Small but full of character, Urbanna overflows with a vibrant community that cherishes its marine environment. Located by the Rappahannock River, the city has a well-established boating industry. Visitors passing by can learn more about this rich culture and history at the Urbanna Museum with popular exhibits like “The Oyster is King" and the 1755 Mitchell Map that played an important role in the Revolutionary War. Beyond the museum, there are other outdoor activities like the Urbanna Creek Walk to enjoy the beautiful scenery by the Rappahannock River. Anglers favor this river for fishing, which tempts the community with many attractions like the Urbanna Oyster Festival that happens yearly.

The Takeaway

All these towns share Chesapeake Bay's beauty equally, but it is up to you to decide where you want to begin your adventure. Most travelers tend to visit multiple towns along the body of water as a road trip. All of these towns by the waterfront are filled with rich culture, fun activities, and an awe-inspiring view of nature. 

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